diethyl [11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate | 268227-42-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl [11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate
• 英文别名: 11-diethoxyphosphorylundecyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS: 268227-42-5
• 化学式: C₂₀H₃₆NO₈P
• 分子量: 449.481
• InChiKey: UDPAQIFJZNRXLB-UHFFFAOYSA-N

物化性质

• 沸点：
  528.9±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  30.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl [11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis

  摘要：

  The question whether phage display can be used as a selection method in the directed evolution of enantioselective enzymes has not been answered satisfactorily to date. In order to be able to test this in a specific case, namely in the hydrolytic kinetic resolution of the acetate derived from alpha,beta- isopropylideneglycerol (IPG) catalyzed by the lipase from Bacillus subtilis, suicide enzyme inhibitors anchored on porous glass or polymer beads were designed and synthesized. These are immobilized phosphonates, which bear a leaving group and also contain the chiral substrate (D) and (L)-IPG, Modified SIRAN((R)) (porous glass) and Tentagel((R)) (polymer) were chosen as carriers, attachment occurring via amide-forming coupling or Ru-catalyzed olefin metathesis. Initial lipase inhibition studies are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01052-9
• 作为产物：
  描述：

  11-溴-1-十一醇 在 硫酸 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 0.5h， 生成 diethyl [11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate
  参考文献：
  名称：

  A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes

  摘要：

  A bifunctional activity label (8) for directed molecular evolution of lipolytic enzymes has been designed and synthesized. The structure is composed of a 4-nitrophenyl activated phosphonate, that is, a suicide substrate of lipases/esterases, connected to a biotin moiety through a spacer containing a disulfide bridge. The phosphonate (3) was prepared by Michaelis-Arbuzov reaction of trimethylsilyl-protected 11-bromoundecanol (2) with triethyl phosphite. The deprotected omega-hydroxyalkylphosphonate (4) was transformed into an active N-hydroxysuccinimide carbonate (5) followed by 4-nitrophenyl activation of the phosphonate using standard procedures. The biotinylated phosphonate inhibitor (8) was then synthesised by coupling the phosphonate inhibitor (6) to the E-amino-caproic acid and cystamine containing biotinyl spacer (7). The function of all relevant groups of the final activity label (8) (biotin-label, cleavable disulfide bridge, phosphonate-inhibitor) have been successfully tested with the commercial lipase Lipolase(R) (Novo Nordisk). Hence, a tool for directed molecular evolution of lipolytic enzymes has been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00002-x

文献信息

• A novel biotinylated suicide inhibitor for directed molecular evolution of lipolytic enzymes
  作者：H.-J. Deussen、S. Danielsen、J. Breinholt、T.V. Borchert

  DOI：10.1016/s0968-0896(00)00002-x

  日期：2000.3

  A bifunctional activity label (8) for directed molecular evolution of lipolytic enzymes has been designed and synthesized. The structure is composed of a 4-nitrophenyl activated phosphonate, that is, a suicide substrate of lipases/esterases, connected to a biotin moiety through a spacer containing a disulfide bridge. The phosphonate (3) was prepared by Michaelis-Arbuzov reaction of trimethylsilyl-protected 11-bromoundecanol (2) with triethyl phosphite. The deprotected omega-hydroxyalkylphosphonate (4) was transformed into an active N-hydroxysuccinimide carbonate (5) followed by 4-nitrophenyl activation of the phosphonate using standard procedures. The biotinylated phosphonate inhibitor (8) was then synthesised by coupling the phosphonate inhibitor (6) to the E-amino-caproic acid and cystamine containing biotinyl spacer (7). The function of all relevant groups of the final activity label (8) (biotin-label, cleavable disulfide bridge, phosphonate-inhibitor) have been successfully tested with the commercial lipase Lipolase(R) (Novo Nordisk). Hence, a tool for directed molecular evolution of lipolytic enzymes has been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Immobilization of chiral enzyme inhibitors on solid supports by amide-forming coupling and olefin metathesis
  作者：Manfred T Reetz、Carsten J Rüggeberg、Melloney J Dröge、Wim J Quax

  DOI：10.1016/s0040-4020(02)01052-9

  日期：2002.10

  The question whether phage display can be used as a selection method in the directed evolution of enantioselective enzymes has not been answered satisfactorily to date. In order to be able to test this in a specific case, namely in the hydrolytic kinetic resolution of the acetate derived from alpha,beta- isopropylideneglycerol (IPG) catalyzed by the lipase from Bacillus subtilis, suicide enzyme inhibitors anchored on porous glass or polymer beads were designed and synthesized. These are immobilized phosphonates, which bear a leaving group and also contain the chiral substrate (D) and (L)-IPG, Modified SIRAN((R)) (porous glass) and Tentagel((R)) (polymer) were chosen as carriers, attachment occurring via amide-forming coupling or Ru-catalyzed olefin metathesis. Initial lipase inhibition studies are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.